Spray an 8"-x-8" baking dish with cooking spray and line with parchment, leaving a 2-inch overhang on two sides. Spray the parchment with cooking spray.

Make the Caramel: In a heatproof medium bowl, microwave caramels over high until melted, stirring every 30 seconds, about 2 minutes total. Carefully, (the bowl will be hot) pour caramel mixture into the prepared baking dish and smooth top with a spatula. Let sit at room temperature, do not refrigerate.

Make the Marshmallow: In a stand mixer, whisk the gelatin with 1/3 cup water and let sit.
In a small saucepan, combine sugar with corn syrup and 1/4 cup of water and bring to a boil, stirring occasionally. Cook over moderate heat, without stirring, until the sugar syrup registers between 240° and 250°on a candy thermometer, about 6 minutes.
Carefully drizzle the hot syrup down the side of the stand mixer bowl, while beating at medium-low speed.

Add vanilla and a large pinch of salt and beat at high speed until thick and glossy, about 4 minutes.

Quickly scrape the marshmallow mixture on top of the caramel and smooth with a spatula. Let sit at room temperature, at least 1 hour.

Using the parchment overhang, lift the caramel and marshmallow out of the pan and cut into squares.

Line a rimmed baking sheet with parchment paper. Using a fork, dip each candy square into the melted chocolate, then set on the prepared baking sheet.

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